Intracranial haemorrhage is a rare, high-risk complication in patients with end-stage liver disease, lacking established neurosurgical guidelines, especially when a living donor is available for urgent liver transplantation. We present a challenging case of a 39-year-old man with acute-on-chronic liver failure who developed two episodes of subdural haemorrhage with midline shift within one week. He was initially stabilised with burr hole evacuation but required a decompression craniectomy following a recurrence. Despite these crises, he successfully underwent living donor LT within a month. His complex post-transplant course included hepatic artery thrombosis, a cerebrospinal fluid leak, and sinking flap syndrome, all managed successfully. This report underscores the critical role of a multidisciplinary team in making timely decisions and navigating the delicate balance between bleeding and thrombotic risks in managing ICH in LT candidates.